Urethane compound, curable composition containing the same, and cured product thereof

Abstract

It is an object of the present invention to provide a urethane compound capable of providing a cured product which is excellent in surface hardness, scratch resistance, flexibility and bending property, has reduced curling property and also has good transparency, a curable composition containing the same and a cured product thereof. The curable composition of the present invention is characterized by containing a specific urethane compound having an isocyanurate ring skeleton and a polymerization initiator.

1 . A urethane compound represented by the following general formula (1): 
       
         
           
           
               
               
           
         
         wherein R 1  is a straight-chain or branched divalent aliphatic group of 1 to 12 carbon atoms, a divalent organic group of 3 to 12 carbon atoms having an alicyclic group, a divalent organic group having an aromatic ring or [—(CH 2 ) a —O—(CH 2 ) b ] c  (a and b are each independently an integer of 1 to 10, and c is an integer of 1 to 5), 
         R 2  is a straight-chain or branched divalent aliphatic group of 1 to 10 carbon atoms, a divalent organic group of 3 to 10 carbon atoms having an alicyclic group, a divalent organic group having an aromatic ring or [—(CH 2 ) d —O—(CH 2 ) e —] f  (d and e are each independently an integer of 1 to 10, and f is an integer of 1 to 5), and 
         R 3  is a hydrogen atom or a methyl group. 
       
     
     
         2 . The urethane compound as claimed in  claim 1 , wherein in the general formula (1), R 1  is a divalent aliphatic group of 1 to 6 carbon atoms,
 R 2  is a divalent saturated aliphatic group of 1 to 6 carbon atoms, a divalent organic group having an benzene ring or [—(CH 2 ) d —O—(CH 2 ) e —] f  (d and e are each independently an integer of 1 to 5, and f is an integer of 1 to 3), and   R 3  is a hydrogen atom.   
     
     
         3 . A curable composition containing the urethane compound (A) as claimed in  claim 1  and a polymerization initiator (B). 
     
     
         4 . The curable composition as claimed in  claim 3 , further containing a urethane oligomer (C). 
     
     
         5 . The curable composition as claimed in  claim 3 , further containing a reactive monomer (D). 
     
     
         6 . The curable composition as claimed in  claim 3 , further containing a thiol compound (E). 
     
     
         7 . The curable composition as claimed in  claim 6 , wherein the thiol compound (E) has two or more structures represented by the following general formula (2): 
       
         
           
           
               
               
           
         
       
       wherein R 8  and R 9  are each independently a hydrogen atom, an alkyl of 1 to 10 carbon atoms or an aryl group, m is an integer of 0 to 2, n is 0 or 1, and R 8  and R 9  are not hydrogen atoms at the same time. 
     
     
         8 . The curable composition as claimed in  claim 3 , further containing a urethane compound (F) represented by the following general formula (3): 
       
         
           
           
               
               
           
         
       
       wherein R 4  is a straight-chain or branched divalent aliphatic group of 1 to 12 carbon atoms, a divalent organic group of 3 to 12 carbon atoms having an alicyclic group, a divalent organic group having an aromatic ring or [—(CH 2 ) g —O—(CH 2 ) h —] i  (g and h are each independently an integer of 1 to 10, and i is an integer of 1 to 5),
 R 5  is a straight-chain or branched divalent aliphatic group of 1 to 10 carbon atoms, a divalent organic group of 3 to 10 carbon atoms having an alicyclic group, a divalent organic group having an aromatic ring or [—(CH 2 ) p —O—(CH 2 ) q —] r  (p and q are each independently an integer of 1 to 10, and r is an integer of 1 to 5), and 
 R 6  and R 7  are each independently a hydrogen atom or a methyl group. 
 
     
     
         9 . A paint comprising the curable composition as claimed in  claim 3 . 
     
     
         10 . An adhesive comprising the curable composition as claimed in  claim 3 . 
     
     
         11 . A cured product obtained by curing the curable composition as claimed in  claim 3 . 
     
     
         12 . A coating material obtained by curing the curable composition as claimed in  claim 3 . 
     
     
         13 . An optical film obtained by curing the curable composition as claimed in  claim 3 .